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Substance Name: Scopolamine
RN: 51-34-3
UNII: DL48G20X8X
InChIKey: STECJAGHUSJQJN-FWXGHANASA-N
Note
- An alkaloid from SOLANACEAE, especially DATURA and SCOPOLIA. Scopolamine and its quaternary derivatives act as antimuscarinics like ATROPINE, but may have more central nervous system effects. Its many uses include an anesthetic premedication, the treatment of URINARY INCONTINENCE and MOTION SICKNESS, an antispasmodic, and a mydriatic and cycloplegic.
Molecular Formula
- C17-H21-N-O4
Molecular Weight
- 303.3559
- All
- Classifications
- Links to Resources
- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
Classification Codes
- Adjuvants, Anesthesia
- Antiemetics
- Antiviral (COVID-19)
- Autonomic Agents
- Central Nervous System Agents
- Cholinergic Agents
- Cholinergic Antagonists
- Drug / Therapeutic Agent
- Gastrointestinal Agents
- Human Data
- Muscarinic Antagonists
- Mutation Data
- Mydriatics
- Neurotransmitter Agents
- Peripheral Nervous System Agents
- Reproductive Effect
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Names and Synonyms
Name of Substance
- Scopolamine
MeSH Heading
- Scopolamine
Synonyms
- (-)-Hyoscine
- (-)-Scopolamine
- 1alphaH,5alphaH-Tropan-3alpha-ol, 6beta,7beta-epoxy-, (-)-tropate (ester)
- 3-Oxa-9-azatricyclo(3.3.1.0(sup 2,4))nonan-7-ol, 9-methyl-, tropate (ester)
- 3-Oxa-9-azatricyclo(3.3.1.O(sup 2,4))nonan-7-ol, 9-methyl-, tropate (ester)
- 6,7-Epoxytropine tropate
- 6-beta,7-beta-Epoxy-3-alpha-tropanyl S-(-)-tropate
- 6beta,7beta-Epoxy-1alpha,5alpha-tropan-3alpha-ol
- 6beta,7beta-Epoxy-3alpha-tropanyl S-(-)-tropate
- alpha-(Hydroxymethyl)benzeneacetic acid 9-methyl-3-oxa-9-azatricyclo(3.3.1.0(2.4))non-7-yl ester
- Atrochin
- Atroquin
- Boro-Scopol
- EC 200-090-3
- EINECS 200-090-3
- Epoxytropine tropate
- HSDB 4074
- Hydrobromicum, Scopolaminum
- Hyoscine
- Hyosol
- Isopto Hyoscine
- l-Scopolamine
- Oscine
- Scopace
- Scopine (-)-tropate
- Scopine tropate
- SEE
- Skopolamin
- Transderm SCOP
- Transderm-Scop
- Tropic acid, 9-methyl-3-oxa-9-azatricyclo(3.3.1.0(sup 2,4))non-7-yl ester
- Tropic acid, ester with scopine
- UNII-DL48G20X8X
Systematic Names
- Benzeneacetic acid, alpha-(hydroxymethyl)-, (1alpha,2beta,4beta,5alpha,7beta)-9-methyl-3-oxa-9-azatricyclo(3.3.1.02,4)non-7-yl ester, (alphaS)-
- Benzeneacetic acid, alpha-(hydroxymethyl)-, 9-methyl-3-oxa-9-azatricyclo(3.3.1.02,4)non-7-yl ester, (7(S)-(1alpha,2beta,4beta,5alpha,7beta))-
- Hyoscine
- Scopolamine
Registry Numbers
CAS Registry Number
- 51-34-3
FDA UNII
- DL48G20X8X
Other Registry Numbers
- 14797-94-5
- 226562-00-1
- 28901-63-5
- 58670-87-4
- 65319-33-7
- 97991-84-9
System Generated Number
- 0000051343
Structure Descriptors
InChI
InChI=1S/C17H21NO4/c1-18-13-7-11(8-14(18)16-15(13)22-16)21-17(20)12(9-19)10-5-3-2-4-6-10/h2-6,11-16,19H,7-9H2,1H3/t11-,12-,13-,14+,15-,16+/m1/s1InChIKey
STECJAGHUSJQJN-FWXGHANASA-NSmiles
CN1[C@@H]2C[C@H](C[C@H]1[C@@H]3O[C@H]23)Toxicity
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| human | TDLo | intramuscular | 4ug/kg (0.004mg/kg) | SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" | "Possible Long-Term Health Effects of Short-Term Exposure to Chemical Agents," National Research Council, 3 vols., Washington, DC, National Academy Press, 1982-85Vol. 1, Pg. L1, 1982. |
| human | TDLo | subcutaneous | 2ug/kg (0.002mg/kg) | BEHAVIORAL: EXCITEMENT BRAIN AND COVERINGS: CHANGES IN SURFACE EEG BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" | Journal of Pharmacology and Experimental Therapeutics. Vol. 137, Pg. 133, 1962. |
| man | TDLo | intramuscular | 24ug/kg (0.024mg/kg) | BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" | Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 32, Pg. 250, 1973. |
| man | TDLo | subcutaneous | 14ug/kg (0.014mg/kg) | BEHAVIORAL: ATAXIA BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" | American Journal of Psychiatry. Vol. 141, Pg. 1010, 1984. |
| mouse | LD50 | intraperitoneal | 400mg/kg (400mg/kg) | BEHAVIORAL: EXCITEMENT BEHAVIORAL: IRRITABILITY SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE | Arzneimittel-Forschung. Drug Research. Vol. 21, Pg. 1727, 1971. |
| mouse | LD50 | intravenous | 100mg/kg (100mg/kg) | Journal of Medicinal Chemistry. Vol. 26, Pg. 1772, 1983. | |
| mouse | LD50 | oral | 1275mg/kg (1275mg/kg) | BEHAVIORAL: REGIDITY BEHAVIORAL: TREMOR | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 134, Pg. 255, 1961. |
| mouse | LD50 | subcutaneous | 1700mg/kg (1700mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 56, Pg. 85, 1936. | |
| rabbit | LDLo | intravenous | 50mg/kg (50mg/kg) | "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935. | |
| rabbit | LDLo | subcutaneous | 75mg/kg (75mg/kg) | "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935. | |
| rat | LD50 | oral | 2650mg/kg (2650mg/kg) | Farm Chemicals Handbook. Vol. -, Pg. C272, 1991. | |
| women | TDLo | subcutaneous | 13ug/kg (0.013mg/kg) | BEHAVIORAL: ATAXIA BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" | American Journal of Psychiatry. Vol. 141, Pg. 1010, 1984. |
Physical Properties
| Physical Property | Value | Units | Temp (deg C) | Source |
|---|---|---|---|---|
| Melting Point | 59 | deg C | EXP | |
| pKa Dissociation Constant | 7.75 | (none) | 25 | EXP |
| log P (octanol-water) | 0.98 | (none) | EXP | |
| Water Solubility | 1.00E+05 | mg/L | EXP | |
| Vapor Pressure | 7.18E-09 | mm Hg | 25 | EST |
| Henry's Law Constant | 3.36E-16 | atm-m3/mole | 25 | EST |
| Atmospheric OH Rate Constant | 5.97E-11 | cm3/molecule-sec | 25 | EST |
Physical property data is provided to ChemIDplus by SRC, Inc.